I'm in DII and already had two of my three guys "considering us" for several periods, and although they hadn't signed, I decided to go ahead and try to fill my last spot with the money I had left - with the third guy also being a "pull down/drop down."

I put in about $3,500 on him, but then see that, although he's been "considering us" for FOURTEEN straight cycles, another owner has decided to challenge me for one of my recruits. I put my focus there, fight him off and keep the recruit. However, this has left me with no money to continue trying to "pull down" the third recruit who I had spent $3,500 on.

He has told me all the things they normally tell you when you're a backup option, but my question is this.... even though I don't have anymore money to spend on him, will he eventually drop down to me since we are now into signings and coming up on the last day and no one else has tried to recruit him? Or is he just going to forget my $3,500 and go to a SIM AI school or JUCO at the end of recruiting?

That's happened to me.  If you don't have anyone else on his list, just wait for him to sign.  Your chances are pretty good.

Really? Right now he's not even considering us is the problem. Been about six cycles since I last put money into him. You think if no one else recruits him he will eventually "considering us" and then sign with me?

I think that if you were not able to get him to consider you and you don't have money when he drops to give him a little more effort to get him to consider you he will probably never sign with you.

As long as you gave him a scholarship and no one else tries to recruit him, you should be fine. I signed a dropdown at the last minute with little money. It never said considering me, but he still signed at one of the last recruiting cycles.

They will sign without ever considering you.  Especially if they are drop downs and no one else comes after them.  I have also had them not sign and go juco when I had offered them the sun, moon and all the playing time they wanted.  Most likely to sign though based on my experience.